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Enterprise Software Thread, Upgrading Exchange 2003 to 2013 hybrid with O365 in Technical; Hi guys. We need to upgrade our ageing 2003 install and have decided, for a variety of reasons (mostly due ...
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    Upgrading Exchange 2003 to 2013 hybrid with O365

    Hi guys.

    We need to upgrade our ageing 2003 install and have decided, for a variety of reasons (mostly due to the 30GB mailbox storage you get) to go with Office 365 with an exchange 2013 server on-site.

    The reason for having an on-site exchange server, as far as I understand it, is greater manageability (I know you can create remote PSSessions with O365 but it doesn't have the same/as many cmdlets) and also the easier management of users and distribution groups. I may be wrong about all my assumptions so far, so please correct me if I am wrong

    Now, I understand upgrading from 2003 to 2013 is a hassle, but my question is what would an upgrade path look like for a 2003 to 2013 O365 hybrid setup? Do we migrate 2003-2013 first then set up the 365/azure/ADFS?

    Also, we are looking at salamander (something which apparently takes information out of facility and puts it into AD...not examined at it in detail but I don't like the look of it) so if anyone has any experience with that it would be good to hear...

    Thanks for any comments

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    SYNACK's Avatar
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    I would go from 2003 to 2010 to 2013 then enable hybrid, there is no direct path from 2003 to 2013 without a bunch of downtime and hassle for you and users.

    Biggest thing with ADFS is certificates and IP addresses, you need an external IP assigned to a DNS name you have a cert for, generally best to just get a wildcard cert if you can swing it.
    Last edited by SYNACK; 25th July 2014 at 05:41 PM.

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    Thanks for the reply.

    The move from 2003 to 2013 isn't my biggest concern to be honest. There are third party solutions (codetwo) for about £50 that will (allegedly) migrate everything over with a few clicks.

    Does anyone have experience with hybrid deployments? Does having on site dirsync and exchange servers increase manageability enough to be worth it? I have trawled through technet but can't seem to find concrete answers.

    Thanks again!

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    Quote Originally Posted by SYNACK View Post
    Biggest thing with ADFS is certificates and IP addresses, you need an external IP assigned to a DNS name you have a cert for, generally best to just get a wildcard cert if you can swing it.
    You will also need that for the on premise exchange server. Although ADFS is much less hassle.

    Quote Originally Posted by fxlite View Post
    Does anyone have experience with hybrid deployments? Does having on site dirsync and exchange servers increase manageability enough to be worth it? I have trawled through technet but can't seem to find concrete answers.
    We have a Exchange 2013 and Office 365 Hybrid. We will soon be ditching the on premise Exchange 2013. There is no need for it. Your users and groups can be done in active directory and then DirSync moves that to the could. Thats what we do. What are you trying to achieve exactly by having the on premise box? If anything having that makes things more complex.

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    By the way you get 50GB not 30GB

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    Quote Originally Posted by FN-GM View Post
    You will also need that for the on premise exchange server. Although ADFS is much less hassle.
    You just need a single cert for exchange and you can remap everything to go through mail.whatever.org.country it is not ideal but doable. You can even stack ADFS and exchange all on the same ssl cert and external ip but it is quite a hack so it's much better to spend the extra stack of money to make it work as MS intended (with no regard to how non-fourtune 500 companies get their internet).

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    A certificate isn't expensive really, just a pain sometimes to sort them out. Not sure about NZ but here in the UK its easier to get external IP's than it was in Australia.

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    Quote Originally Posted by FN-GM View Post
    A certificate isn't expensive really, just a pain sometimes to sort them out. Not sure about NZ but here in the UK its easier to get external IP's than it was in Australia.
    Nightmare or impossible to get extra IPs here depending on ISP and technology, stuff like DSL and it is impossible without a whole separate connection just for an IP. Certs are still $300-$400 minimum per year that actually work with more than a couple of browsers, that may seem small to you but it is just another cost making these 'free' services like Office365 not actually free, it becomes very difficult once the school has been sold by advertising on the 'free' nature of something to then turn around and get them to fork out $300 per year on SSL and more (maybe $70 per month) for an additional IP, $100 to get student advantage actually activated, and then time to design a VLE or something useable in a school in SharePoint. We are still doing that but it is an uphill battle when money keeps getting involved for these things on a (promoted as) free service.

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    Thanks for the reply - I actually have a small business 365 account and forgot it was 50GB! God knows who actually has a mailbox that big...

    After reading a bit more I am slowly subscribing to the belief that an on-site exchange server is largely unnecessary. I think our rationale was that, since we would have to move to either exchange 2010 SP3 or 2013 to even start with O365, we might as well retain an on-premise exchange server given that A: a hybrid license is apparently free and B: our thoughts were that it would be easier (or safer) to have two solutions in place in case we went for a phased upgrade (moving users across in chunks) or in case something else went pear shaped.

    Oh, I've just looked at the manageability side again on my 365 account and realised it seems to be possible to use all the exchange 2013 cmdlets on O365 (I thought it was only the cmdlets in the MSOnline module that were available).

    edit - I'll have to check how many IPs we've got and how many we're currently using for stuff...we have a wildcard cert so I don't see ADFS being a huge issue.
    Last edited by fxlite; 26th July 2014 at 01:26 PM.

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